Happy fall fashion week. We hope that you are fashion-forward during these next several days, and wish you the best of luck in sparking a brief romance with a lonely stylist’s assistant before the week is out.

In honor of this most festive of weeks, we have compiled a somewhat comprehensive guide to the best gear from the past twenty years’ worth of skate videos. Skateboarding didn’t just begin “embracing fashion,” as some misinformed outfits have recently reported. Fashion has been stealing shit from skaters for years. (Luckily, they left Javier Nunez’s City Stars jeans alone.) Here’s the proof: All the jerseys, sweats, camo, braids, insane patches, sweater vests and swooshy pants that you could ever hope for. Yes, there are omissions. No, it isn’t in order. Thanks to Roctakon, Boss Bauer, Sweet Waste, Jack Sabback and Jason from Frozen in Carbonite for their contributions to this post.

Biebel has a career-long allegiance to the most gargantuan clothing imaginable, but no piece in any of his parts has come close to the size the sweatpants he wore for the half cab crook on the Barcelona theater ledge. For a video full of unnecessary slow-mo, this was the only point in Fully Flared where regular-speed was absolutely unacceptable.

I wore khaki cargos for years after this video because of Gino, but Gino was accessible. He looked like me. This guy looked like he was from another planet. The Brotha From Anotha Planet that we all desperately wanted to inhabit, but could not. He looks like he’s skating only because someone put a board in front of him, and he was just like, “Fuck it.” Kareem styled on every other skater in a video packed with gods. In my mind, this line did as much for Adidas shell toes in the nineties as Run DMC did the decade before. And don’t even get me started on the line he does in K Swiss. — Roctakon

The Hawaiian / all-over-printed button-up shirt is one of skateboarding’s most underutilized classic looks. The G Man was documented wearing one by a notable fashion blogger as early as yesterday, and Quim Cardona did it great justice almost twenty years ago.

In an episode of Epicly Later’d, Carroll talks about being young and living without parental supervision. The legendary braids and this flawless outfit from that era are the ultimate what-could-have-been. Carroll obviously grew up into a normal adult person and the skate world is probably better for it. But imagine if he got more into rapping and psychedelics, and less into being one of the most prolific skaters of all time. — Roctakon

Canadian skaters’ forays into gear coordination usually look like poor attempts at channeling Rob Welsh and late-nineties Love Park style pioneers. Many skaters have worn jerseys to pay homage to their favorite teams, but Wade Desarmo crushed the jersey game by wearing Jason Kidd jersey jeans, justifiably making him the only Canadian on this list.

Dill has been through more than a handful of #stylez in his twenty-year career: nineties tech gear / pants with drawstring bottom hems, Helmut Lang jeans and Supreme hoodies, being early to the earthtone party that began raging after Mosiac came out, a homeless-looking phase, and a lot of high socks, to name a few. Normally, wallrides don’t go with basketball shorts, but he somehow made it work in his most easy-to-miss, dressed-down-yet-fashion-forward moment.

While creating this list, we agreed to limit our thirty choices to prominent professional skateboarders. Then we remembered that James Frankhouse wore a pink Phillies jersey with a matching fitted and hemp Dunks in a Cincinnati shop video, and realized there had to be one exception.

Good grey denim is hard to find and not often seen in skate videos. For a four-minute section filled with style icons (Stevie, Maurice Key, James Kelch, Henry Sanchez), Mike Graham found a good-enough pair, and neglected the rich history of his hometown basketball franchise (Simple equation: Boston skaters = Boston jerseys) by opting for Sir Charles’ Phoenix jersey.

Biebel’s Fully Flared sweats were probably 4XL. Eddie Rap Life’s banana-yellow quilted jacket was at least 5XL, likely making it the largest piece of clothing to be worn by someone in a skate video. Don’t forget that he had on Carolina blue Dunks to match the jacket’s hems and cuffs.

In addition to making one of the greatest observations about skateboarding ever (“If 50 Cent skated, he would skate the Pier”), Andy Honen proved you don’t need yellow, Carolina blue or wild colors in general to coordinate a great outfit for a line. With simply a white tee, black sweats, black and white DCs and a black and white bucket hat (the hat really tied it together), he showed how monochrome goes long way.

Many people remember Harold for getting naked and waving his dick around in Kids, but he was pretty great at dressing, too. With one Washington Square Park line, he encapsulated the fashion of the entire mid-90s: a yellow Nautica pullover jacket, baggy black carpenter jeans (likely Guess or something like it), and some Fila sneakers.

There is no other skater (besides maybe Carroll and Rick) that could pull off a sweater vest. It’d be safe to assume that while filming for Yeah Right, Gino decided to see if he could bring 360 shove-its back from the dead, possibly get people doing fakie varial flips, usher in acceptance for burgundy chinos, and see to the wildcard possibility of popularizing sweater vests. One of those didn’t work out, but three-out-of-four is pretty good.

In the wildly competitive world of 2000s Bay Area jersey-wearing skateboarders, it became evident that surpassing Rob Welsh was practically impossible. If you can’t out-skate him at the Pier, then you out-gear him. Brad Johnson left major league teams behind and opted for an incredible oversized Hooters baseball jersey, permanently inching him a notch above every other skater to ever wear a jersey at Pier 7. (P.S. He also does a line in baby blue Air Force Ones.)

Scott Johnston was always a subtly well-dressed white guy, so he deserves mention on this list despite no particularly outlandish #stylez in his catalog. However, it’s worth noting that he skated in Evisu jeans several years before they would eventually burst in popularity, and usher in a trend of absolutely horrendous back pocket designs and ridiculous price tags. (Shout out to Red Monkey.)

***NOTE: Someone just e-mailed us saying that the 5050 in Evisu jeans was Ty Evans, not Scott Johnston. Either way, S.J. belongs on this list.

Camo pants have been a standard fixture in skate videos for a long time, but the patterns are usually limited to straightforward woodland. In Time Code, Kalis brought out black and white camo shorts, one of the most all-around uncommon camo patterns. If only he could’ve borrowed Andy Honen’s bucket hat. Honorable mention goes to the grey sweats with the mesh pocket from Photosynthesis, and always rocking a Yankees hat despite being more closely-associated with Philadelphia.

I was there. Not for the banger in Timbs, but I was on the sidelines at Pulaski watching as he filmed his legendary Fine Artists part. Me and my friends saved for weeks and scoured discount stores looking for the exact CK jeans that he wore. When we found them, or the cheap Silver Tab copies, we rubbed the bottoms with old grip tape trying to get that perfect Pepe cuff. And when we met girls, we tried to hug them casually and steal a kiss the way he did. If you didn’t grow up on the east coast, you’ll never understand that throwing down in Timbs is not some wacky thing done for a laugh. It’s some shit that happened randomly, when you’re getting nice before Soul Camp, just kicking it, and not even expecting to skate. — Roctakon

Lavar is permanently the best little kid skater because of 1) Obviously his skating 2) Less obviously, his gear. Little kids now live and die by the Krew rack at their local shop, or whatever awful graphic tees come in their flow box. Lavar was like 13 skating with a watch and Malcolm X “By Any Means Necessary” tee. Supreme would be inspired to release the same exact tee in different colors ten years later. You can’t learn style at the skatepark.

A Rhythm skateboards sweatshirt, Triple 5 Soul cargo pants (likely four sizes too big), and a…Shirt. Tied. Around. His. Head. This outfit earned the illustrious Geo Moya both this clip, and a Platform.net (hip-hop / skate / “urban culture” site from back when the internet was a new thing) ad.

Swooshy pants paired with a backwards hat would make anyone outside of a few Philly skaters and Keenan Milton look like an uncover cop. Though swooshy pants were standard issue for the entire TSA team circa 1998, when you watch footage of them now, most of those dudes look like Union Square ravers that just took up breakdancing. Pulling off swooshy pants is best left to the expertise of black dudes, which is why these two lines from the first Chocolate video are great.

Incentive checks are a big part of being a pro skateboarder, but most pros are too lazy to reach beyond wearing a tee, hat or throwing a few stickers on their board. Good thing Javier found a loophole and put a gigantic City Stars patch on his already gigantic pants to match the logo on his shirt.

Before Anthony Pappalardo singlehandedly caused the commodity stock of brown chino fabric to explode into a multi-billion dollar industry, he was seen flossing in European airports with a more refined appreciation of brown gear by way of a Louis Vuitton duffle bag. Nike Air Maxes go great with Louie, too.

Much like Pappalardo, Puleo’s pre-brown pants / cellar door career phase is buried history. Had he continued to skate with a cuban link chain, skateboarder enrollment at Pratt these past ten years would have been lower, Slap message board topics containing the word “Puleo” would rarely have surpassed two pages, and less white kids would still be editing skate clips to KRS-One.

Sad made a name for himself in skateboard fashion by turning something as mundane as a white hand towel into a trademark accessory. Lucas Puig even paid homage to in a recent Adidas clip. But beyond the towel, his finest exercise in accessorizing came in the form of a big booty girl / condom / pager trifecta while wearing a Grind King shirt in his 411 “Rookies” intro. “No time for slippin’.”

Baggy gear on skaters is nothing new, but notable San Diego-based designer, Peter Smolik, was the first to harmoniously fuse together the “fashion” of baggy pants with their significantly more troublesome “function.” The tradeoff with baggy pants is that they are bound to drag on the floor and get torn up. That is, until Smolik and the scientists at Osiris came around, and invented the O.D.S.S.A.G. no-drag system, which hooked the hems of baggy pants to his signature Osiris shoe, allowing you to sag, wear pants that are six sizes too big, and not suffer the consequences.

He’s wearing some of the ugliest Airwalks ever made and a t-shirt promoting the lesser half of EPMD. He should look like a jackass, but somehow, he looks perfect. This is what’s missing in skating today. You look at this guy and think, “This dude’s probably gonna get me arrested, make me hold his weed when we get popped boosting Polo khakis from Macy’s, but I don’t care, I’d give anything for us to be crew.” — Roctakon

According to Wikipedia, “The Raider organization does not retire the jersey numbers of former players on an official or unofficial basis.” If that policy ever changes, #80 should be retired for Rob Welsh, because at this point, it’s just as much of a skateboard jersey as a football one.

Blow-up athletic company logo tees were big amongst the non-caucasian skater crowd in the nineties. Marcus McBride wore an Adidas one, Keenan repped Fila and Nike Air (while wearing shell toes, oddly enough), and Jahmal repped Tommy Hilfiger, presumably within a year (at most) span of when Only Built 4 Cuban Linx came out and propelled the Tommy brand to new heights.

and yes, as I was scrolling down the list – I found myself thinking “If Pepe’s ‘Fine Artist’ part isn’t mentioned – I’m going to have to cut a b*tch”. Amazing comment by Rocktacon. Couldn’t have said it better myself. Pepe was an equally huge skate fashion/style influence on me and my friends. What an amazing place (the east coast) and moment in time (early/mid 90’s) for skating that was. ‘Fine Artists Vol. 1’ was to me what Photosynthesis is for most of the slightly younger heads on this website. The red (or royal blue) Qur’an.

Was about to post about Eli Reed’s green getup then saw the first comment hahaha. And another nod for Scott Johnston, he’s always had well put together outfits. I remember times when I’ve said that a skateboarder’s outfit can have a big impact on their style and people have looked at me like I’m crazy. Look at how great all of Rob Welsh’s shit looks because of his gully clothes, and how bad Tom Penny looks now that he’s wearing so much cotton, you can’t actually see what his body is doing.

Speaking of which, High 5 era Penny should have had a mention for the clean cut preppy look, but it doesn’t really fit with the swagtastic theme running through this post.

i flashed back to the 90’s seeing these dudes skate the banks, water st, astor place, union sq, ect ect. Vinny ponte taught me how to do a derby ollie over pot holes downtown. I had the sickest ollie ever from then on.

Smolik hat over a Real hoodie is classic. But let’s not forget the muska’s visor beenie. I hear by state it now that this whole SnapBack 90’s thing will die soon to prevail the baggy late 90’s and the dreaded 00’s look.

i wonder though, having read roctacock’s paragrapgh about reem and fully fucking hi fiving and punching the sky, are we left to ignore the KCK’S?
20 shot was amazing. reem was from another fucking planet in that video. and he did come to murder us earthlings. but in trilogy he wrote letters to the clink and told to shiloh stay up and think of westerns. reeem was still not relateable to me. except for some fuckin reason he started skating for fucking duffs and single handedly killed all skate shoes…. untill this day everyones mad they got styled on by him. at least according to my undying perminant opinion. duffs as a shoe line was pretty much the shittiestly designed line of shoes ever made save for the shit that the other steve olsen skated for and late 90’s/2000’s vans. not a hip hop shoe or a skate shoe has done it since(except for games’s hurricanes which i bought hoping to channel the kck’s and kind of did….actaully the hurricanes were an exact bite of the reems). and the revamped axions kinda sorta had it. granted he skated in all shoes in every video part but the fact that he made a shitty white mans dumby shoe line look astronomically exceptable in most of his next part may warrent a next episode in this exemplary display of phat sylez. KCK’S is the law.

Pretty thorough list. If you were to expand to include outfits captured in print I would nominate Spencer Fujimoto’s color coordination with the green-yellow highlights on his DCs, shirt, and board. I think it was in a Slap… maybe an interview… possibly a heelfip varial off a bump. Pretty futuristic for it’s time.

I agree with Manute and Snack’s latest replies. I think the transition that happened to skating in the interim between 20 Shot Sequence and Trilogy is something that happens, sometimes several times over, in any subculture. It’s the point where people from within the subculture start producing goods and clothing that had previously been re-purposed from outside sources. KCK’s, Menace, Droors, DC, Osiris (list goes on) were responding to the times: skaters were starting to dress ‘fresh’ / ‘hip hop’ / ‘urban’ / whatever you want to call it.
Prior to the late 90’s, everyone had to wear actual Polo, Tommy Hill, Nautica etc etc – and also had to wear shoes that were not actually meant for skating (sometimes pretty difficult to skate in, at that) – like Nike GTS, Stan Smiths, Shell toes, various Reeboks and Nike x-trainers etc etc… don’t get me started on the puffy tounge/multiple inserted tounge craze (I’m looking at you, 90’s philly skaters)

I think it’s cool that skating keeps up and sometimes even dictates fashion trends, but sometimes when everything starts getting ripped off and reproduced, the quality can fall off. I mean, let’s face it – designer clothing labels have much more know-how and production levels than the average start-up skate clothing company.
So unfortunately, the skate industry left to its own devices can easily start to churn out loads of incredibly bad gear that passes for Urban wear… things can get ugly real quick. I believe that’s what we started seeing in the Triology era.

I think this piece is perfect as is, with possibly the exception of including of anything Steve Olson ever wore, whether the afore-mentioned Shorty’s era Crazy Monk or his Foundation days Buddy-Holly-goes-to-a-rave outfits.

Tom Penny is not and has never been hip hop at all. he’s a european that dresses kooky. And as I said before, you can lean everything you need to know about bastien by watching the video part where he skates to Black Eye Peas.

argueing about a once godlike and now completely fucked brit and a frenchie that has gnar on lock but always turns backside is redundant.
its not about washed out bums treflipping at macba, its about phatstylez

Pepe Martinez definitely, and totally like Roctakon said…I tell this story all the time…Pep came up to me at MLK in DC and asked to use my board…he was wearing the army hat with a drawstring (which could have used a mention in here somewhere, better than the Honen bucket hat) a wifebeater, cargo shorts and Tims,..instead of stealing my board, he did a kf bs ts on one of the tall ledges, first try no less. RIP.

Ok, my friend and I need some clarification on the Kareem/K Swiss mention?! As a huge world/Kareem/everything nerd it is bugging me/us not to know what this means.

My closest guess – (and I am thinking seriously outside of the fucking KCK box here) is that legendary line where he checks his pager – he is wearing the Menace T shirt with the shield (the Polo version of that is known by Polo heads as the K Swiss range) and perhaps thaaaat is what you mean? Or am I thinking too much about this? Does he just wear some god Lutzka-damn K Swizzles at some point?

I was just talking about kareem skating in K Swiss which he does. Early 90s mad people wore K Swiss. They was a classic look in DC, I don’t really know about elsewhere. I’d guess not in NY, but where I grew up they were sorta like uptowns in that they were standard black or white shoe people wore until they got dirty. Like rebook classics, etc etc

“In the wildly competitive world of 2000s Bay Area jersey-wearing skateboarders, it became evident that surpassing Rob Welsh was practically impossible. If you can’t out-skate him at the Pier, then you out-gear him.”

i love to break it to you all, but Ed Hall AKA Eddie Rap Life and that 4 xl blue jacket, is actually inside out, with yellow interior. you can see the tags, and the lining round the bottom is from the inner jacket. also paul shier/ nick jenson rock the grey sweater vest, but i guess cause they’re British they are a bunch of squares right?

great article dudes…not sure i read any mention of long leather braided belts though which were a big part of hip-hop and skate fashion 94-97. You can clearly see Harold rocking in photo you posted, also Joey Suriel too. Guy wore in a lot of his part in Mouse plus so many more…

Just wanted to point out to the people that give Bastien credit for the T-rag that he just ripped that from Penny. Penny rocked it a lot earlier than Sorry and should of course be mentioned for sometimes wearing 3 t-shirts at once. Sometimes 1 on the head and 2 the regular way but has also been spotted wearing 3 layers of tees to match his shoes. :-)